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527254

Sigma-Aldrich

(Trimethylsilyl)diazomethane solution

2.0 M in diethyl ether

Synonym(s):

TMS-Diazomethane solution, (Diazomethyl)trimethylsilane

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About This Item

Linear Formula:
(CH3)3SiCHN2
CAS Number:
18107-18-1
Molecular Weight:
114.22
Beilstein:
1902903
MDL number:
MFCD00053946
UNSPSC Code:
12352302
PubChem Substance ID:
24874613
NACRES:
NA.22

concentration

2.0 M in diethyl ether

density

0.773 g/mL at 25 °C

storage temp.

2-8°C

SMILES string

C[Si](C)(C)C=[N+]=[N-]

InChI

1S/C4H10N2Si/c1-7(2,3)4-6-5/h4H,1-3H3

InChI key

ONDSBJMLAHVLMI-UHFFFAOYSA-N

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General description

(Trimethylsilyl)diazomethane is considered as a non-explosive substitute to diazomethane for the homologation of carbonyl derivatives, mainly ketones, via reactions such as Tiffeneau-Demjanov rearrangement.

Application

Reactant for preparation of:
  • Macrolactam analogs of the natural product macrolide (-)-A26771B with improved metabolic stability and antibacterial activity
  • Aigialomycin D analogues as protein kinase inhibitors for cancer treatment
  • Unnatural α-amino acid derivatives containing gem-bisphosphonates via Michael addition reaction
  • Capped 4-methylumbelliferyl hyaluronan disaccharides and tetrasaccharides as potential hyaluronidase substrates
  • Stictamides A-C as matrix metallopeptidase 12 (MMP12) inhibitors with antitumor invasion activity
  • Endothelin converting enzyme (ECE) Inhibitors WS 75624A and WS 75624B via a cross-metathesis approach
  • Ent-kaurene derivatives as anti-inflammatory agents
  • Desmosdumotin C analogs as potent antitumor agents acting via activation of spindle assembly checkpoint
  • Imidazolo[2,1-b]benzothiazole derivatives as potential p53 inhibitors

related product

Product No.
Description
Pricing

Signal Word

Danger

Hazard Classifications

Acute Tox. 2 Inhalation - Acute Tox. 4 Oral - Carc. 1B - Flam. Liq. 2 - STOT SE 1 Inhalation - STOT SE 3

Target Organs

Central nervous system, Lungs

Supplementary Hazards

EUH019,EUH066

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

-31.0 °F - closed cup

Flash Point(C)

-35 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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A novel three-step analytical method was developed which enables the simultaneous detection and identification of multifunctional oxygenated products resulting from the reaction of α-pinene with ozone. The method consists of the following steps: conversion of carbonyl groups to methyloximes using
Homologation reaction of ketones with diazo compounds.
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T J van 't Erve et al.
Environment international, 36(8), 835-842 (2010-04-14)
Diazomethane is a highly explosive and toxic gas routinely employed for the quantitative and clean derivatization of phenols. We investigated the commercially available trimethylsilyldiazomethane in the presence of diisopropylethylamine as a safe, non-explosive and less-toxic alternative using six phenolic polychlorinated
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